Cesium carbonate → (S)-tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)pyrrolidine-1-carboxylate

HRID 79304

反応式

HRID 79304 の反応式
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[N:26]=2)[N:4]=1)[CH3:2].CS(O[C@@H:37]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[N:26]=[C:27]([O:31][C@H:41]3[CH2:37][CH2:38][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40]3)[CH:28]=[CH:29][CH:30]=2)[N:4]=1)[CH3:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylateHCID 178437935HCID 178437935、化合物

生成物 1

HCID 70814880(S)-tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)pyrrolidine-1-carboxylate収率 50.6%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
90 °C

実験手順

To N-(3-ethyl-1-((6-hydroxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (21 mg, 0.051 mmol) in DMA (2 mL) was added (R)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate (20 mg, 0.076 mmol) and Cs2CO3 (33 mg, 0.10 mmol). The reaction vial was sealed, and the reaction was heated to 90° C. and stirred for 6 hours. DMA was removed under reduce pressure. The residue was diluted with EtOAc (20 mL), washed with saturated NaHCO3 aqueous solution (5 mL) and brine (5 mL), and concentrated. Silica gel chromatography of the crude material (DCM/MeOH 10:0.5) provided the desired product (15 mg).

後処理

  1. customThe reaction vial was sealed
  2. customDMA was removed
  3. additionThe residue was diluted with EtOAc (20 mL)
  4. washwashed with saturated NaHCO3 aqueous solution (5 mL) and brine (5 mL)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-1885a0e738a94714aea0ffd29319f71a
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

関連ノート

読み込み中…